Dilithium Tetrachlorocuprate(II) Catalyzed Oxidative Homocoupling of Functionalized Grignard Reagents

Si-Kai Hua; Qiu-Peng Hu; Jiangmeng Ren; Bu-Bing Zeng

doi:10.1055/s-0032-1316841

Synthesis, Table of Contents

Synthesis 2013; 45(4): 518-526
DOI: 10.1055/s-0032-1316841

paper

Dilithium Tetrachlorocuprate(II) Catalyzed Oxidative Homocoupling of Functionalized Grignard Reagents

Si-Kai Hua

^bShanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China Fax: +86(21)64253689 Email: renjm@ecust.edu.cn Email: zengbb@ecust.edu.cn

,

Qiu-Peng Hu

^bShanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China Fax: +86(21)64253689 Email: renjm@ecust.edu.cn Email: zengbb@ecust.edu.cn

,

Jiangmeng Ren*

^bShanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China Fax: +86(21)64253689 Email: renjm@ecust.edu.cn Email: zengbb@ecust.edu.cn

,

Bu-Bing Zeng*

^aShanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China

^bShanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China Fax: +86(21)64253689 Email: renjm@ecust.edu.cn Email: zengbb@ecust.edu.cn

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Abstract

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Abstract

An efficient procedure is described for the oxidative homocoupling of functionalized Grignard reagents using a catalytic amount of dilithium tetrachlorocuprate(II) (CuLi₂Cl₄) in the presence of pure oxygen gas. This method is applied successfully to a variety of aryl, heteroaryl, alkyl, alkenyl and alkynyl halides, which are converted into the corresponding homocoupled products in good to excellent yields.

Key words

homocoupling - dilithium tetrachlorocuprate(II) - Grignard reagents - oxidant - metalation

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References

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